Hillsborough

Welcome to Hillsborough

Unlike some Peninsula towns that started out as rough frontier outposts, Hillsborough has always been Hillsborough. Back in 1910, on the eve of its incorporation, one San Francisco newspaper writer called it "the perfumed city." That description still fits.

Hillsborough traces its roots to the Burlingame Country Club, established in 1893 by a group of landowners led by Francis Newlands. Hillsborough was actually on track to become part of Burlingame, until its wealthy residents decided they wanted no part of their neighbor's sidewalks and storefronts. They incorporated on their own on April 25, 1910, with about 750 residents.

Most of Hillsborough's original estates are gone, but a few survive as private homes or institutions. Carolands, the 98-room chateau completed in 1916 for Pullman heiress Harriett Pullman Carolan, is now preserved by the Carolands Foundation, which offers free, docent-led tours by lottery reservation most Wednesdays. Tobin Clark's "House-on-Hill," a 1931 Cotswold-style mansion, remains a private residence. And two other Crocker family estates, W.H. Crocker's Skyfarm and Templeton Crocker's Uplands, are now the campuses of The Nueva School and Crystal Springs Uplands School, respectively.

Hillsborough's zoning still reflects its founders' intentions. City code sets a half-acre minimum lot size, and there are no apartments, condominiums, or townhouses anywhere in town. Other than its four public schools, one park, and a single golf course, there are no businesses at all within Hillsborough's borders, by city law. The founders weren't kidding in 1910 when they said they wanted nothing that would "detract from the rural atmosphere" of their new town.

Schools are a big part of the draw. The Hillsborough City School District includes three elementary schools (North, South, and West) and Crocker Middle School, which was named a California Distinguished School for 2026 and consistently ranks among the top few percent of California middle schools. The Hillsborough Schools Foundation has raised tens of millions of dollars for local schools since it was founded in 1980.

The town takes its traditions seriously. The Memorial Day Parade and Carnival still draws the whole community to Floribunda Avenue each year, and the Hillsborough Concours d'Elegance, now in its 70th year, is recognized as the longest continually running car show of its kind in the world. With a population just under 11,000 and no storefronts to gather around, Hillsborough residents tend to find community in the streets, the schools, and events like these instead.

Hillsborough is a smaller, more private market than most of the Peninsula, and I bring the same approach here that's guided my clients across the Peninsula since 2004: careful preparation, honest advice, and a clear read on how estate lots, architectural pedigree, and privacy factor into value in ways a standard comparable sale doesn't always capture. If you're trying to understand a specific Hillsborough street or estate, or how it compares to Woodside or Atherton, I'm glad to walk you through it.

- Caroline